1-Bromo-3-chloropropane → 3-(3-Chloropropyl)-4-oxothiazolidine

A solution of 4-oxothiazolidine (3.00 g) in tetrahydrofuran (40 ml) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil) (1.28 g) in tetrahydrofuran (30 ml) at room temperature with stirring. 3-Bromo-1-chloropropane (3.15 ml) was added dropwise to the mixture under refluxing and the mixture was allowed to reflux for 9 hours. After the resultant precipitate was removed by filtration, the filtrate was evaporated in vacuo. The residue was chromatographed on basic alumina by eluting with ethyl acetate and then with a 10:1 mixture of toluene and ethyl acetate to give 3-(3-chloropropyl)-4-oxothiazolidine (2.60 g) as colorless oil.

1. temperatureunder refluxing
2. temperatureto reflux for 9 hours
3. customAfter the resultant precipitate was removed by filtration
4. customthe filtrate was evaporated in vacuo
5. customThe residue was chromatographed on basic alumina
6. washby eluting with ethyl acetate
7. additionwith a 10:1 mixture of toluene and ethyl acetate

ORD record

ord-ef698b54e32f40288fd9dc2ea81efb58

Source dataset

uspto-grants-1988_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04764514